Literature DB >> 20055393

NHC catalyzed oxidations of aldehydes to esters: chemoselective acylation of alcohols in presence of amines.

Suman De Sarkar1, Stefan Grimme, Armido Studer.   

Abstract

Not just one but two carbenes of the same structure act cooperatively in oxidative acylations of alcohols with aldehydes by using a readily available cheap organic oxidant. Alcohols are selectively acylated in the presence of amines by cooperative carbene catalysis. Quantum chemical calculations support the suggested mechanism.

Entities:  

Year:  2010        PMID： 20055393     DOI： 10.1021/ja910540j

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  42 in total

Review 1.  Recent advances in site-selective functionalization of carbohydrates mediated by organocatalysts.

Authors:  Stephanie A Blaszczyk; Timothy C Homan; Weiping Tang
Journal:  Carbohydr Res       Date:  2018-11-23       Impact factor: 2.104

2.  Chiral N-heterocyclic carbene-catalyzed generation of ester enolate equivalents from {alpha},{beta}-unsaturated aldehydes for enantioselective Diels-Alder reactions.

Authors:  Juthanat Kaeobamrung; Marisa C Kozlowski; Jeffrey W Bode
Journal:  Proc Natl Acad Sci U S A       Date:  2010-10-25       Impact factor: 11.205

3.  Metal-free chlorodeboronation of organotrifluoroborates.

Authors:  Gary A Molander; Livia N Cavalcanti
Journal:  J Org Chem       Date:  2011-08-03       Impact factor: 4.354

Review 4.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

5.  N-heterocyclic carbene-catalyzed rearrangements of vinyl sulfones.

Authors:  Roxanne L Atienza; Howard S Roth; Karl A Scheidt
Journal:  Chem Sci       Date:  2011-06-10       Impact factor: 9.825

6.  On the role of CO2 in NHC-catalyzed oxidation of aldehydes.

Authors:  Pei-Chen Chiang; Jeffrey W Bode
Journal:  Org Lett       Date:  2011-04-12       Impact factor: 6.005

7.  A Sequential Cycloaddition Strategy for the Synthesis of Alsmaphorazine B Traces a Path Through a Family of Alstonia Alkaloids.

Authors:  Allen Y Hong; Christopher D Vanderwal
Journal:  Tetrahedron       Date:  2016-11-03       Impact factor: 2.457

8.  Pd-catalyzed aldehyde to ester conversion: a hydrogen transfer approach.

Authors:  Brittany A Tschaen; Jason R Schmink; Gary A Molander
Journal:  Org Lett       Date:  2013-01-15       Impact factor: 6.005

9.  Exploiting Acyl and Enol Azolium Intermediates via NHeterocyclic Carbene Catalyzed Reactions of Alpha-Reducible Aldehydes.

Authors:  Harit U Vora; Philip Wheeler; Tomislav Rovis
Journal:  Adv Synth Catal       Date:  2012-04-19       Impact factor: 5.837

Review 10.  A continuum of progress: applications of N-hetereocyclic carbene catalysis in total synthesis.

Authors:  Javier Izquierdo; Gerri E Hutson; Daniel T Cohen; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-16       Impact factor: 15.336
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